Is it permissible for an Orthodox woman to do horseback riding in an ordinary saddle, or does she have to use a sidesaddle? Furthermore, would she be able to use women's trousers made for horseback riding, or does she need to dress in a skirt?

Maria, orthodox Judaism permits the same things for Orthodox women and for other Jewish women (at least in the vast majority of cases). Is there a particular reason you ask whether standard riding would be permissible for, specifically, an Orthodox woman?
– msh210♦Oct 28 '12 at 7:29

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@msh210 a non-orthodox woman is not likely to feel that orthodox understanding of the Halachah is binding on her.
– Seth JOct 28 '12 at 16:33

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@SethJ, but the question was whether it's permissible, not whether the woman views it as such.
– msh210♦Oct 29 '12 at 0:33

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@msh210 Yes, but that depends on whom you ask. If you assume, as many here seem to, that any Halachic discussion must be from the Orthodox perspective, then, sure, it's redundant. But if you don't, it makes sense to specify.
– Seth JOct 29 '12 at 1:33

4 Answers
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Rabbi Barry Freundel (rabbi of Kesher Israel in Washington, DC) said in a Q&A that if a woman is doing an activity more modestly done in pants than a skirt, she should wear women's pants. As examples, he mentioned bicycle riding and mountain climbing. He said there no longer exists an issue of beged ish with women wearing pants.

Should I refrain from answering one because I can't answer the other? One might be able to make a case that riding a horse is no worse than riding a bike, which he explicitly permits.
– Ze'ev misses MonicaOct 28 '12 at 5:34

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Wearing pants is not about beged ish, it's about showing the shape of the legs. So the suggestion is either VERY loose pants, or pants with a skirt on top.
– ArielOct 28 '12 at 6:56

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Too bad my other comment was removed, but this person proved by his own deeds that his rulings, in these subjects especially, should be ignored.
– user6591Jun 21 '15 at 18:30

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@Ze'ev this is not a mathematical equation dependant on logic alone. This is a halachic ruling trying to delicately and ethically balance rules of decency that are not written in stone. This is the epitome of a ruling that depends on the validity of the source.
– user6591Aug 27 '15 at 17:41

Rav Avigdor Nevenzahl in Hanhagos uMinhagim 16 writes there is an inyan for a woman to refrain from riding a horse because of a proof from Rashi (Pesachim daf 3a Rashi Ki Amar) by a woman its written "או על הכלי אשר היא יושבת" since it is not appropriate to mention riding or pisuk reglaim regarding a woman. For this reason it is assur for women to wear pants because of pisuk reglayim aside from other issurim.

It seems riding a horse should not be done,but pants are assur,that's how I understood it,see it inside.

How is pants pisuk raglayim if she is standing? I understand if she is squatting with her legs apart (as she would be if on a horse) then it's pissuk raglayim. But pants by itself isn't.
– Double AA♦Jun 20 '14 at 2:26

I would assume it means the outline is already pisuk reglayim,I do hear the question,but I can see how pants shows the outline too
– samJun 20 '14 at 2:28

But you do understand when one walks in,pants each leg is shown separated as opposed to a skirt or cloak of some sort
– samJun 20 '14 at 2:31

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Perhaps I'm ignorant, but I am unaware of sources before recent times that interpreted the gemara in P'sachim as forbidding wearing pants. Nor am I aware of any non-recent sources (i.e. prior to late Acharonim) who mention this notion of pisuk raglayim (in the manner popularly interpreted by the hamon am in our day) beyond saying that it's indelicate to speak explicitly about a woman riding astride when it is unnecessary.
– FredJun 22 '14 at 5:56

Were the women who taught you halachik experts? Are you?
– Double AA♦Jan 25 '13 at 13:29

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@Carlita, welcome to mi yodeya, and thanks for sharing your experience! This answer would be more valuable if you could edit in your or your teachers' Halachic rationale, communal traditions, or other source for your and their feelings on the subject. Also, please consider registering your account, which will give you access to more of the site's features.
– Isaac Moses♦Jan 25 '13 at 14:43

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Orthodox. I'm not sure that you're using that word the same way many of the users here do.
– Hod - Monica's ArmyJan 28 '13 at 0:09